Pyridine → (But-3-yn-1-yloxy)(tert-butyl)dimethylsilane

HRID 1057796Notes

Reaction equation

HRID 1057796 reaction equation
[CH2:1]([OH:5])[CH2:2][C:3]#[CH:4].[Si:6](Cl)([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7].N1C=CC=CC=1>C(Cl)Cl>[Si:6]([O:5][CH2:1][CH2:2][C:3]#[CH:4])([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7]

Participants

5

Reactant 3

HCID 1049PyridineHCID 135663-Butyn-1-OLHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 4304567(But-3-yn-1-yloxy)(tert-butyl)dimethylsilane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3-butyne-1-ol (5.0 g; 71.3 mmol) in ca. 75 ml of methylene chloride was added tert-butydimethylsilyl chloride (10.8 g; 71.6 mmol) and 7 ml of pyridine. The mixture was allowed to stir overnight at room temperature, diluted with methylene chloride, washed with water, 1M HCl, brine and dried (Na2SO4). Concentration in vacuo afforded the title compound as a colorless liquid.

Workup

  1. washwashed with water, 1M HCl, brine
  2. dry with materialdried (Na2SO4)
  3. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-edfc0f1250e1421b8d5d995f157688c8
Source dataset
uspto-grants-2003_02
Patent number
US06515015B1

Reaction notes

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